# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qyl-a
_database_code_depnum_ccdc_archive 'CCDC 2354055'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2023-07-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 Br O P'
_chemical_formula_sum            'C27 H20 Br O P'
_chemical_formula_weight         471.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9801(3)
_cell_length_b                   17.8286(8)
_cell_length_c                   15.0481(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.601(4)
_cell_angle_gamma                90
_cell_volume                     2089.38(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4888
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2750
_cell_measurement_theta_min      2.9620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7911
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.613
_diffrn_reflns_theta_min         3.900
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  20.00   1.00    1.00    --  -40.73  77.00  90.00   68
  2  ω   -113.00 -14.00   1.00    1.00    --  -40.73 -57.00-180.00   99
  3  ω     38.00  83.00   1.00    1.00    --   40.73-125.00-150.00   45
  4  ω     57.00 132.00   1.00    1.35    --  106.95 -45.00-150.00   75
  5  ω     91.00 129.00   1.00    1.35    --  106.95 -77.00-150.00   38
  6  ω     81.00 171.00   1.00    1.35    --  106.95  30.00  30.00   90
  7  ω    115.00 178.00   1.00    1.35    --  106.95 125.00   0.00   63
  8  ω    102.00 175.00   1.00    1.35    --  106.95 125.00-150.00   73
  9  ω     50.00  87.00   1.00    1.35    --  106.95 -61.00  90.00   37
 10  ω     77.00 107.00   1.00    1.35    --  106.95 -95.00 120.00   30
 11  ω     28.00  56.00   1.00    1.35    --  106.95 -95.00 120.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0535037000
_diffrn_orient_matrix_UB_12      -0.0779770000
_diffrn_orient_matrix_UB_13      0.0404696000
_diffrn_orient_matrix_UB_21      0.0693662000
_diffrn_orient_matrix_UB_22      0.0361742000
_diffrn_orient_matrix_UB_23      0.0940572000
_diffrn_orient_matrix_UB_31      -0.1769866000
_diffrn_orient_matrix_UB_32      -0.0093544000
_diffrn_orient_matrix_UB_33      0.0234100000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3570
_reflns_number_total             4099
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0806P)²+0.6016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.87509(5) 0.60182(2) 0.42002(2) 0.03655(15) Uani 1 1 d . . . . .
P1 P 0.46844(8) 0.64120(4) 0.80487(4) 0.01748(17) Uani 1 1 d . . . . .
O1 O 0.5971(3) 0.67429(12) 0.88097(13) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.3854(3) 0.70983(15) 0.71714(18) 0.0198(5) Uani 1 1 d . . . . .
C2 C 0.4474(4) 0.78260(16) 0.7312(2) 0.0244(6) Uani 1 1 d . . . . .
H2 H 0.526478 0.795180 0.786078 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3938(4) 0.83684(17) 0.6653(2) 0.0294(6) Uani 1 1 d . . . . .
H3 H 0.436314 0.886629 0.674931 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2786(4) 0.81865(17) 0.5854(2) 0.0277(6) Uani 1 1 d . . . . .
H4 H 0.244459 0.855685 0.539583 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2127(4) 0.74665(18) 0.5719(2) 0.0270(6) Uani 1 1 d . . . . .
H5 H 0.131393 0.734614 0.517602 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2660(4) 0.69207(17) 0.63788(19) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.220857 0.642661 0.628899 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2751(4) 0.61164(15) 0.84031(19) 0.0211(6) Uani 1 1 d . . . . .
C8 C 0.2504(4) 0.64176(17) 0.9217(2) 0.0266(6) Uani 1 1 d . . . . .
H8 H 0.333914 0.674710 0.955707 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1051(5) 0.6241(2) 0.9534(2) 0.0366(8) Uani 1 1 d . . . . .
H9 H 0.089578 0.644216 1.009515 0.044 Uiso 1 1 calc R U . . .
C10 C -0.0175(4) 0.5770(2) 0.9029(3) 0.0380(8) Uani 1 1 d . . . . .
H10 H -0.117853 0.565065 0.924254 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0055(4) 0.54704(19) 0.8212(2) 0.0336(7) Uani 1 1 d . . . . .
H11 H -0.079019 0.514746 0.786800 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1515(4) 0.56426(17) 0.7900(2) 0.0266(6) Uani 1 1 d . . . . .
H12 H 0.167377 0.543727 0.734168 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5463(3) 0.56089(15) 0.75019(18) 0.0186(5) Uani 1 1 d . . . . .
C14 C 0.6199(3) 0.57147(15) 0.67041(18) 0.0185(5) Uani 1 1 d . . . . .
C15 C 0.6783(4) 0.64179(16) 0.6474(2) 0.0227(6) Uani 1 1 d . . . . .
H15 H 0.663925 0.684202 0.683192 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7554(4) 0.65132(17) 0.5747(2) 0.0253(6) Uani 1 1 d . . . . .
H16 H 0.793436 0.699371 0.560182 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7761(4) 0.58849(18) 0.5230(2) 0.0245(6) Uani 1 1 d . . . . .
C18 C 0.7277(4) 0.51867(17) 0.54462(19) 0.0239(6) Uani 1 1 d . . . . .
H18 H 0.745157 0.476891 0.508521 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6517(3) 0.50782(15) 0.62008(19) 0.0204(5) Uani 1 1 d . . . . .
C20 C 0.6149(3) 0.43335(15) 0.6498(2) 0.0212(6) Uani 1 1 d . . . . .
C21 C 0.5692(3) 0.42490(16) 0.7348(2) 0.0223(6) Uani 1 1 d . . . . .
C22 C 0.5405(3) 0.49063(16) 0.78662(19) 0.0213(6) Uani 1 1 d . . . . .
C23 C 0.5115(4) 0.47814(18) 0.8813(2) 0.0268(6) Uani 1 1 d . . . . .
H23A H 0.397477 0.456257 0.877386 0.040 Uiso 1 1 calc R U . . .
H23B H 0.519004 0.526186 0.913584 0.040 Uiso 1 1 calc R U . . .
H23C H 0.599249 0.443853 0.914499 0.040 Uiso 1 1 calc R U . . .
C24 C 0.5410(4) 0.35188(17) 0.7649(2) 0.0286(6) Uani 1 1 d . . . . .
H24 H 0.512561 0.345613 0.822503 0.034 Uiso 1 1 calc R U . . .
C25 C 0.5537(4) 0.29005(17) 0.7132(2) 0.0326(7) Uani 1 1 d . . . . .
H25 H 0.531922 0.241553 0.734295 0.039 Uiso 1 1 calc R U . . .
C26 C 0.5990(4) 0.29857(17) 0.6289(2) 0.0315(7) Uani 1 1 d . . . . .
H26 H 0.608496 0.255691 0.592872 0.038 Uiso 1 1 calc R U . . .
C27 C 0.6300(4) 0.36893(17) 0.5981(2) 0.0272(6) Uani 1 1 d . . . . .
H27 H 0.661974 0.373997 0.541215 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C17 1.902(3) . ?
P1 O1 1.483(2) . ?
P1 C1 1.816(3) . ?
P1 C7 1.817(3) . ?
P1 C13 1.827(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.391(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(4) . ?
C7 C12 1.391(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.459(4) . ?
C13 C22 1.372(4) . ?
C14 C15 1.407(4) . ?
C14 C19 1.418(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(4) . ?
C17 C18 1.364(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.412(4) . ?
C19 C20 1.452(4) . ?
C20 C21 1.413(4) . ?
C20 C27 1.407(4) . ?
C21 C22 1.453(4) . ?
C21 C24 1.412(4) . ?
C22 C23 1.509(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C25 1.365(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.401(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(5) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 112.00(13) . . ?
O1 P1 C7 112.20(13) . . ?
O1 P1 C13 114.40(12) . . ?
C1 P1 C7 102.14(13) . . ?
C1 P1 C13 107.86(12) . . ?
C7 P1 C13 107.40(13) . . ?
C2 C1 P1 117.2(2) . . ?
C2 C1 C6 119.9(3) . . ?
C6 C1 P1 122.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 P1 116.1(2) . . ?
C8 C7 C12 119.6(3) . . ?
C12 C7 P1 124.3(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C14 C13 P1 120.5(2) . . ?
C22 C13 P1 119.4(2) . . ?
C22 C13 C14 120.1(2) . . ?
C15 C14 C13 122.1(3) . . ?
C15 C14 C19 118.3(3) . . ?
C19 C14 C13 119.2(2) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.3(3) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.1(3) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 Br1 118.4(2) . . ?
C18 C17 Br1 119.9(2) . . ?
C18 C17 C16 121.8(3) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C20 119.7(3) . . ?
C18 C19 C14 118.6(3) . . ?
C18 C19 C20 121.6(3) . . ?
C21 C20 C19 119.1(3) . . ?
C27 C20 C19 121.9(3) . . ?
C27 C20 C21 118.9(3) . . ?
C20 C21 C22 120.1(3) . . ?
C24 C21 C20 118.6(3) . . ?
C24 C21 C22 121.2(3) . . ?
C13 C22 C21 119.9(3) . . ?
C13 C22 C23 122.5(3) . . ?
C21 C22 C23 117.5(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24 119.1 . . ?
C25 C24 C21 121.7(3) . . ?
C25 C24 H24 119.1 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C20 C27 H27 119.5 . . ?
C26 C27 C20 120.9(3) . . ?
C26 C27 H27 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C17 C18 C19 -179.1(2) . . . . ?
P1 C1 C2 C3 177.6(2) . . . . ?
P1 C1 C6 C5 -177.5(2) . . . . ?
P1 C7 C8 C9 178.5(2) . . . . ?
P1 C7 C12 C11 -177.7(2) . . . . ?
P1 C13 C14 C15 18.1(4) . . . . ?
P1 C13 C14 C19 -169.1(2) . . . . ?
P1 C13 C22 C21 167.7(2) . . . . ?
P1 C13 C22 C23 -14.6(4) . . . . ?
O1 P1 C1 C2 -0.8(3) . . . . ?
O1 P1 C1 C6 178.5(2) . . . . ?
O1 P1 C7 C8 17.7(3) . . . . ?
O1 P1 C7 C12 -164.8(2) . . . . ?
O1 P1 C13 C14 -92.9(2) . . . . ?
O1 P1 C13 C22 84.9(2) . . . . ?
C1 P1 C7 C8 -102.4(2) . . . . ?
C1 P1 C7 C12 75.1(3) . . . . ?
C1 P1 C13 C14 32.5(2) . . . . ?
C1 P1 C13 C22 -149.7(2) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
C2 C3 C4 C5 1.7(5) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C6 C1 C2 C3 -1.8(4) . . . . ?
C7 P1 C1 C2 119.4(2) . . . . ?
C7 P1 C1 C6 -61.2(3) . . . . ?
C7 P1 C13 C14 141.9(2) . . . . ?
C7 P1 C13 C22 -40.3(2) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C7 C12 C11 -0.4(4) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C7 -0.1(5) . . . . ?
C12 C7 C8 C9 0.9(4) . . . . ?
C13 P1 C1 C2 -127.6(2) . . . . ?
C13 P1 C1 C6 51.8(3) . . . . ?
C13 P1 C7 C8 144.3(2) . . . . ?
C13 P1 C7 C12 -38.3(3) . . . . ?
C13 C14 C15 C16 176.8(3) . . . . ?
C13 C14 C19 C18 -178.2(2) . . . . ?
C13 C14 C19 C20 -1.6(4) . . . . ?
C14 C13 C22 C21 -14.5(4) . . . . ?
C14 C13 C22 C23 163.2(3) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C14 C19 C20 C21 -8.2(4) . . . . ?
C14 C19 C20 C27 174.4(3) . . . . ?
C15 C14 C19 C18 -5.1(4) . . . . ?
C15 C14 C19 C20 171.5(2) . . . . ?
C15 C16 C17 Br1 177.8(2) . . . . ?
C15 C16 C17 C18 -2.3(4) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C18 C19 C14 2.8(4) . . . . ?
C17 C18 C19 C20 -173.8(3) . . . . ?
C18 C19 C20 C21 168.3(2) . . . . ?
C18 C19 C20 C27 -9.1(4) . . . . ?
C19 C14 C15 C16 3.9(4) . . . . ?
C19 C20 C21 C22 7.0(4) . . . . ?
C19 C20 C21 C24 -177.2(3) . . . . ?
C19 C20 C27 C26 178.1(3) . . . . ?
C20 C21 C22 C13 4.5(4) . . . . ?
C20 C21 C22 C23 -173.3(3) . . . . ?
C20 C21 C24 C25 -1.3(4) . . . . ?
C21 C20 C27 C26 0.7(4) . . . . ?
C21 C24 C25 C26 1.3(5) . . . . ?
C22 C13 C14 C15 -159.7(3) . . . . ?
C22 C13 C14 C19 13.1(4) . . . . ?
C22 C21 C24 C25 174.5(3) . . . . ?
C24 C21 C22 C13 -171.2(3) . . . . ?
C24 C21 C22 C23 10.9(4) . . . . ?
C24 C25 C26 C27 -0.3(5) . . . . ?
C25 C26 C27 C20 -0.7(5) . . . . ?
C27 C20 C21 C22 -175.6(3) . . . . ?
C27 C20 C21 C24 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.088
_oxdiff_exptl_absorpt_empirical_full_min 0.604
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_27-sd
_database_code_depnum_ccdc_archive 'CCDC 2354056'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-02-01
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 F O P'
_chemical_formula_sum            'C27 H20 F O P'
_chemical_formula_weight         410.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1019(2)
_cell_length_b                   13.6934(3)
_cell_length_c                   12.1992(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.695(2)
_cell_angle_gamma                90
_cell_volume                     2020.72(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5058
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4010
_cell_measurement_theta_min      3.6160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.533
_diffrn_reflns_theta_min         4.856
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  61.00   1.00    1.00    --   40.73 -38.00   0.00   27
  2  ω     50.00  75.00   1.00    1.00    --   40.73-125.00 -30.00   25
  3  ω     36.00 113.00   1.00    1.00    --  106.95-125.00-120.00   77
  4  ω     38.00 136.00   1.00    1.00    --  106.95 -61.00   0.00   98
  5  ω    136.00 162.00   1.00    1.00    --  106.95  45.00  30.00   26
  6  ω    113.00 166.00   1.00    1.00    --  106.95 125.00  60.00   53
  7  ω    146.00 171.00   1.00    1.00    --  106.95 125.00  30.00   25
  8  ω    109.00 162.00   1.00    1.00    --  106.95 125.00 120.00   53
  9  ω     99.00 134.00   1.00    1.00    --  106.95 125.00  30.00   35
 10  ω     80.00 146.00   1.00    1.00    --  106.95  30.00-180.00   66
 11  ω   -112.00 -19.00   1.00    1.00    --  -40.73 -38.00-150.00   93
 12  ω   -112.00 -17.00   1.00    1.00    --  -40.73 -38.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0396823000
_diffrn_orient_matrix_UB_12      -0.0119335000
_diffrn_orient_matrix_UB_13      -0.1204579000
_diffrn_orient_matrix_UB_21      -0.0590981000
_diffrn_orient_matrix_UB_22      0.0993944000
_diffrn_orient_matrix_UB_23      0.0050486000
_diffrn_orient_matrix_UB_31      0.1055946000
_diffrn_orient_matrix_UB_32      0.0512737000
_diffrn_orient_matrix_UB_33      -0.0378952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3590
_reflns_number_total             3965
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+0.4154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.27372(3) 0.33916(3) 0.35152(3) 0.01793(15) Uani 1 1 d . . . . .
O1 O 0.28258(10) 0.25555(9) 0.42947(10) 0.0257(3) Uani 1 1 d . . . . .
F2 F 0.50704(10) 0.02014(8) 0.31244(11) 0.0437(3) Uani 1 1 d . . . . .
C1 C 0.54163(17) 0.56165(14) 0.12804(16) 0.0320(4) Uani 1 1 d . . . . .
H1 H 0.488772 0.612471 0.134448 0.038 Uiso 1 1 calc R U . . .
C2 C 0.64224(18) 0.58152(15) 0.08250(17) 0.0381(5) Uani 1 1 d . . . . .
H2 H 0.658972 0.645968 0.059431 0.046 Uiso 1 1 calc R U . . .
C3 C 0.71904(16) 0.50712(17) 0.07045(16) 0.0374(5) Uani 1 1 d . . . . .
H3 H 0.788377 0.520989 0.039388 0.045 Uiso 1 1 calc R U . . .
C4 C 0.69543(15) 0.41421(15) 0.10298(15) 0.0315(4) Uani 1 1 d . . . . .
H4 H 0.748069 0.363823 0.092668 0.038 Uiso 1 1 calc R U . . .
C5 C 0.59383(14) 0.39165(13) 0.15183(14) 0.0236(4) Uani 1 1 d . . . . .
C6 C 0.51616(14) 0.46699(13) 0.16520(13) 0.0228(4) Uani 1 1 d . . . . .
C7 C 0.41313(13) 0.44814(12) 0.21978(13) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.39570(13) 0.35899(12) 0.26828(13) 0.0186(3) Uani 1 1 d . . . . .
C9 C 0.47317(13) 0.27842(12) 0.25205(13) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.56894(13) 0.29404(13) 0.19014(13) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.63885(15) 0.21442(15) 0.16811(16) 0.0312(4) Uani 1 1 d . . . . .
H11 H 0.701373 0.224722 0.124269 0.037 Uiso 1 1 calc R U . . .
C12 C 0.61932(16) 0.12267(15) 0.20803(17) 0.0348(5) Uani 1 1 d . . . . .
H12 H 0.667269 0.069664 0.193195 0.042 Uiso 1 1 calc R U . . .
C13 C 0.52666(16) 0.11030(13) 0.27100(16) 0.0306(4) Uani 1 1 d . . . . .
C14 C 0.45409(15) 0.18305(13) 0.29245(15) 0.0256(4) Uani 1 1 d . . . . .
H14 H 0.390816 0.170039 0.334353 0.031 Uiso 1 1 calc R U . . .
C15 C 0.25446(13) 0.44947(12) 0.43095(13) 0.0213(3) Uani 1 1 d . . . . .
C16 C 0.15809(15) 0.50502(14) 0.42738(15) 0.0292(4) Uani 1 1 d . . . . .
H16 H 0.098130 0.486736 0.379703 0.035 Uiso 1 1 calc R U . . .
C17 C 0.14944(18) 0.58707(16) 0.49336(18) 0.0393(5) Uani 1 1 d . . . . .
H17 H 0.083913 0.625298 0.490373 0.047 Uiso 1 1 calc R U . . .
C18 C 0.23669(19) 0.61316(16) 0.56367(18) 0.0406(5) Uani 1 1 d . . . . .
H18 H 0.230786 0.669439 0.608666 0.049 Uiso 1 1 calc R U . . .
C19 C 0.33221(17) 0.55768(16) 0.56862(16) 0.0367(5) Uani 1 1 d . . . . .
H19 H 0.391743 0.575811 0.616906 0.044 Uiso 1 1 calc R U . . .
C20 C 0.34091(14) 0.47542(14) 0.50286(15) 0.0283(4) Uani 1 1 d . . . . .
H20 H 0.406080 0.436751 0.506981 0.034 Uiso 1 1 calc R U . . .
C21 C 0.15943(13) 0.32297(12) 0.25478(14) 0.0202(3) Uani 1 1 d . . . . .
C22 C 0.05561(14) 0.30183(13) 0.29474(15) 0.0276(4) Uani 1 1 d . . . . .
H22 H 0.044795 0.301278 0.371554 0.033 Uiso 1 1 calc R U . . .
C23 C -0.03203(15) 0.28157(15) 0.22261(18) 0.0336(4) Uani 1 1 d . . . . .
H23 H -0.103020 0.268138 0.250233 0.040 Uiso 1 1 calc R U . . .
C24 C -0.01680(15) 0.28077(14) 0.11053(17) 0.0335(4) Uani 1 1 d . . . . .
H24 H -0.077172 0.266965 0.061425 0.040 Uiso 1 1 calc R U . . .
C25 C 0.08638(17) 0.30011(16) 0.07046(16) 0.0363(5) Uani 1 1 d . . . . .
H25 H 0.097252 0.299003 -0.006332 0.044 Uiso 1 1 calc R U . . .
C26 C 0.17434(15) 0.32118(15) 0.14227(15) 0.0295(4) Uani 1 1 d . . . . .
H26 H 0.245205 0.334461 0.114284 0.035 Uiso 1 1 calc R U . . .
C27 C 0.32958(15) 0.53039(13) 0.21813(15) 0.0265(4) Uani 1 1 d . . . . .
H27A H 0.256196 0.504142 0.233017 0.040 Uiso 1 1 calc R U . . .
H27B H 0.327981 0.561734 0.145887 0.040 Uiso 1 1 calc R U . . .
H27C H 0.350462 0.578561 0.274435 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4901(12) . ?
P1 C8 1.8365(16) . ?
P1 C15 1.8133(17) . ?
P1 C21 1.8051(16) . ?
F2 C13 1.358(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(3) . ?
C1 C6 1.410(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.416(2) . ?
C5 C6 1.408(2) . ?
C5 C10 1.451(2) . ?
C6 C7 1.454(2) . ?
C7 C8 1.375(2) . ?
C7 C27 1.513(2) . ?
C8 C9 1.465(2) . ?
C9 C10 1.418(2) . ?
C9 C14 1.417(2) . ?
C10 C11 1.411(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 C14 1.359(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(2) . ?
C15 C20 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(2) . ?
C21 C26 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(3) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C8 115.00(7) . . ?
O1 P1 C15 107.87(7) . . ?
O1 P1 C21 111.23(7) . . ?
C15 P1 C8 106.89(7) . . ?
C21 P1 C8 105.64(8) . . ?
C21 P1 C15 110.10(8) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 120.95(18) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.92(19) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.39(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.15(18) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C10 121.85(16) . . ?
C6 C5 C4 118.66(17) . . ?
C6 C5 C10 119.48(15) . . ?
C1 C6 C7 120.59(16) . . ?
C5 C6 C1 118.89(16) . . ?
C5 C6 C7 120.49(15) . . ?
C6 C7 C27 116.33(15) . . ?
C8 C7 C6 119.93(15) . . ?
C8 C7 C27 123.74(14) . . ?
C7 C8 P1 120.33(12) . . ?
C7 C8 C9 120.22(14) . . ?
C9 C8 P1 119.43(12) . . ?
C10 C9 C8 119.65(15) . . ?
C14 C9 C8 122.38(15) . . ?
C14 C9 C10 117.92(15) . . ?
C9 C10 C5 119.42(15) . . ?
C11 C10 C5 121.29(16) . . ?
C11 C10 C9 119.28(16) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.02(18) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 121.3 . . ?
C11 C12 C13 117.33(17) . . ?
C13 C12 H12 121.3 . . ?
F2 C13 C12 118.04(16) . . ?
F2 C13 C14 118.28(18) . . ?
C14 C13 C12 123.67(18) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.72(17) . . ?
C13 C14 H14 120.1 . . ?
C16 C15 P1 124.00(13) . . ?
C20 C15 P1 116.33(13) . . ?
C20 C15 C16 119.59(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.11(17) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.87(19) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.35(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.86(18) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.19(17) . . ?
C19 C20 H20 119.9 . . ?
C22 C21 P1 118.61(13) . . ?
C26 C21 P1 121.90(13) . . ?
C26 C21 C22 119.16(16) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.08(17) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.44(18) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.76(17) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.08(19) . . ?
C26 C25 H25 120.0 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.47(18) . . ?
C25 C26 H26 119.8 . . ?
C7 C27 H27A 109.5 . . ?
C7 C27 H27B 109.5 . . ?
C7 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C8 C9 C10 -178.43(11) . . . . ?
P1 C8 C9 C14 4.2(2) . . . . ?
P1 C15 C16 C17 178.22(15) . . . . ?
P1 C15 C20 C19 -178.63(14) . . . . ?
P1 C21 C22 C23 -175.04(14) . . . . ?
P1 C21 C26 C25 174.35(16) . . . . ?
O1 P1 C8 C7 -159.74(12) . . . . ?
O1 P1 C8 C9 21.52(15) . . . . ?
O1 P1 C15 C16 -113.34(15) . . . . ?
O1 P1 C15 C20 63.49(15) . . . . ?
O1 P1 C21 C22 51.61(16) . . . . ?
O1 P1 C21 C26 -121.74(15) . . . . ?
F2 C13 C14 C9 178.90(15) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C6 C7 C8 -171.47(16) . . . . ?
C1 C6 C7 C27 9.1(2) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C2 C1 C6 C7 175.81(17) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C10 -177.93(17) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C4 C5 C6 C7 -176.97(15) . . . . ?
C4 C5 C10 C9 171.17(15) . . . . ?
C4 C5 C10 C11 -8.1(3) . . . . ?
C5 C6 C7 C8 6.4(2) . . . . ?
C5 C6 C7 C27 -172.99(15) . . . . ?
C5 C10 C11 C12 176.89(17) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C6 C5 C10 C9 -7.5(2) . . . . ?
C6 C5 C10 C11 173.20(16) . . . . ?
C6 C7 C8 P1 172.60(12) . . . . ?
C6 C7 C8 C9 -8.7(2) . . . . ?
C7 C8 C9 C10 2.8(2) . . . . ?
C7 C8 C9 C14 -174.56(15) . . . . ?
C8 P1 C15 C16 122.47(15) . . . . ?
C8 P1 C15 C20 -60.70(15) . . . . ?
C8 P1 C21 C22 177.03(14) . . . . ?
C8 P1 C21 C26 3.68(17) . . . . ?
C8 C9 C10 C5 5.3(2) . . . . ?
C8 C9 C10 C11 -175.39(15) . . . . ?
C8 C9 C14 C13 177.31(16) . . . . ?
C9 C10 C11 C12 -2.4(3) . . . . ?
C10 C5 C6 C1 179.71(16) . . . . ?
C10 C5 C6 C7 1.8(2) . . . . ?
C10 C9 C14 C13 -0.1(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 F2 -179.09(17) . . . . ?
C11 C12 C13 C14 1.6(3) . . . . ?
C12 C13 C14 C9 -1.8(3) . . . . ?
C14 C9 C10 C5 -177.16(15) . . . . ?
C14 C9 C10 C11 2.1(2) . . . . ?
C15 P1 C8 C7 -40.04(15) . . . . ?
C15 P1 C8 C9 141.22(12) . . . . ?
C15 P1 C21 C22 -67.91(15) . . . . ?
C15 P1 C21 C26 118.74(15) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 0.9(3) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
C21 P1 C8 C7 77.21(14) . . . . ?
C21 P1 C8 C9 -101.54(13) . . . . ?
C21 P1 C15 C16 8.20(18) . . . . ?
C21 P1 C15 C20 -174.97(13) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C26 C21 C22 C23 -1.5(3) . . . . ?
C27 C7 C8 P1 -8.0(2) . . . . ?
C27 C7 C8 C9 170.70(15) . . . . ?

_olex2_date_sample_data_collection 2024-02-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.326
_oxdiff_exptl_absorpt_empirical_full_min 0.484
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_26-xd
_database_code_depnum_ccdc_archive 'CCDC 2354059'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-02-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C F3 O3 S, C21 H26 O P'
_chemical_formula_sum            'C23 H27 Cl3 F3 O4 P S'
_chemical_formula_weight         593.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2309(2)
_cell_length_b                   22.3914(4)
_cell_length_c                   12.3597(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.861(2)
_cell_angle_gamma                90
_cell_volume                     2709.69(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6648
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6810
_cell_measurement_theta_min      3.9210
_shelx_estimated_absorpt_T_max   0.598
_shelx_estimated_absorpt_T_min   0.534
_exptl_absorpt_coefficient_mu    4.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11093
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_min         3.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00  72.00   1.00    1.00    --   40.73  57.00 -90.00   58
  2  ω     93.00 173.00   1.00    1.40    --  107.58  45.00 -60.00   80
  3  ω    147.00 178.00   1.00    1.40    --  107.58 125.00  90.00   31
  4  ω    115.00 150.00   1.00    1.40    --  107.58 125.00 120.00   35
  5  ω     94.00 172.00   1.00    1.40    --  107.58 125.00   0.00   78
  6  ω     79.00 174.00   1.00    1.40    --  107.58  61.00-180.00   95
  7  ω     35.00  88.00   1.00    1.40    --  107.58 -94.00  60.00   53
  8  ω     32.00 109.00   1.00    1.40    --  107.58 -94.00 120.00   77
  9  ω      2.00  54.00   1.00    1.00    --   40.73 -99.00 -30.00   52
 10  ω     25.00  78.00   1.00    1.00    --   40.73-125.00-180.00   53
 11  ω    -65.00  32.00   1.00    1.00    --  -40.73  38.00  60.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0841024000
_diffrn_orient_matrix_UB_12      0.0529614000
_diffrn_orient_matrix_UB_13      -0.0235293000
_diffrn_orient_matrix_UB_21      0.0688442000
_diffrn_orient_matrix_UB_22      -0.0417351000
_diffrn_orient_matrix_UB_23      -0.0661784000
_diffrn_orient_matrix_UB_31      -0.1136880000
_diffrn_orient_matrix_UB_32      0.0138454000
_diffrn_orient_matrix_UB_33      -0.1096393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4715
_reflns_number_total             5355
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1173P)²+1.8356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O1, C7
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
3. Uiso/Uaniso restraints and constraints
O1 \\sim C7: within 2A with sigma of 0.0003 and sigma for terminal atoms of
0.0006 within 2A
4.a Ternary CH refined with riding coordinates:
 C23(H23), C16(H16), C19(H19)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.01605(10) 0.75743(4) -0.02622(7) 0.0418(3) Uani 1 1 d . . . . .
Cl2 Cl 0.24214(10) 0.80404(6) 0.11233(11) 0.0617(4) Uani 1 1 d . . . . .
Cl3 Cl 0.08850(10) 0.72385(5) 0.20865(8) 0.0519(3) Uani 1 1 d . . . . .
C23 C 0.0776(3) 0.78097(15) 0.1097(3) 0.0307(7) Uani 1 1 d . . . . .
H23 H 0.029118 0.815662 0.131521 0.037 Uiso 1 1 calc R U . . .
S1 S 0.76349(6) 0.60594(3) 0.68725(6) 0.0192(2) Uani 1 1 d . . . . .
F1 F 0.6278(3) 0.70024(11) 0.5914(2) 0.0632(8) Uani 1 1 d . . . . .
F2 F 0.7499(2) 0.71500(10) 0.7605(2) 0.0496(6) Uani 1 1 d . . . . .
F3 F 0.5635(2) 0.66609(11) 0.7296(2) 0.0551(7) Uani 1 1 d . . . . .
O2 O 0.6664(2) 0.57131(10) 0.60362(19) 0.0329(5) Uani 1 1 d . . . . .
O3 O 0.8804(2) 0.62546(12) 0.6559(2) 0.0398(6) Uani 1 1 d . . . . .
O4 O 0.7923(2) 0.58337(10) 0.80035(18) 0.0292(5) Uani 1 1 d . . . . .
C22 C 0.6715(3) 0.67512(14) 0.6920(3) 0.0288(6) Uani 1 1 d . . . . .
P1 P 0.50425(6) 0.57972(3) 0.22119(5) 0.0127(2) Uani 1 1 d . . . . .
O1 O 0.49625(19) 0.65877(9) 0.01596(16) 0.0205(4) Uani 1 1 d . U . . .
C1 C 0.3603(3) 0.59509(12) 0.1033(2) 0.0175(5) Uani 1 1 d . . . . .
C2 C 0.2309(3) 0.56991(14) 0.0940(3) 0.0254(6) Uani 1 1 d . . . . .
H2 H 0.219733 0.542936 0.149926 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1211(3) 0.58463(16) 0.0033(3) 0.0314(7) Uani 1 1 d . . . . .
H3 H 0.034117 0.567571 -0.003362 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1368(3) 0.62422(16) -0.0783(3) 0.0324(7) Uani 1 1 d . . . . .
H4 H 0.060007 0.634607 -0.139729 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2625(3) 0.64865(14) -0.0713(3) 0.0281(6) Uani 1 1 d . . . . .
H5 H 0.272874 0.675548 -0.127661 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3746(3) 0.63341(12) 0.0197(2) 0.0184(5) Uani 1 1 d . . . . .
C7 C 0.6206(3) 0.63962(12) 0.0814(2) 0.0200(4) Uani 1 1 d . U . . .
C8 C 0.6423(3) 0.60434(11) 0.1735(2) 0.0157(5) Uani 1 1 d . . . . .
C9 C 0.7823(3) 0.58309(12) 0.2374(2) 0.0181(5) Uani 1 1 d . . . . .
C10 C 0.8417(3) 0.59974(14) 0.3498(3) 0.0254(6) Uani 1 1 d . . . . .
H10 H 0.796651 0.627655 0.384578 0.030 Uiso 1 1 calc R U . . .
C11 C 0.9661(3) 0.57572(15) 0.4108(3) 0.0318(7) Uani 1 1 d . . . . .
H11 H 1.005896 0.586972 0.487453 0.038 Uiso 1 1 calc R U . . .
C12 C 1.0323(3) 0.53526(15) 0.3600(3) 0.0325(7) Uani 1 1 d . . . . .
H12 H 1.116940 0.518422 0.402265 0.039 Uiso 1 1 calc R U . . .
C13 C 0.9758(3) 0.51930(15) 0.2482(3) 0.0303(7) Uani 1 1 d . . . . .
H13 H 1.022181 0.492077 0.213207 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8511(3) 0.54316(14) 0.1871(3) 0.0234(6) Uani 1 1 d . . . . .
H14 H 0.812272 0.532117 0.110232 0.028 Uiso 1 1 calc R U . . .
C15 C 0.6230(3) 0.48229(13) 0.3574(3) 0.0268(6) Uani 1 1 d . . . . .
H15A H 0.712227 0.487105 0.343937 0.040 Uiso 1 1 calc R U . . .
H15B H 0.610608 0.440483 0.375674 0.040 Uiso 1 1 calc R U . . .
H15C H 0.618396 0.507806 0.420573 0.040 Uiso 1 1 calc R U . . .
C16 C 0.5104(3) 0.50020(12) 0.2512(2) 0.0183(5) Uani 1 1 d . . . . .
H16 H 0.421697 0.489767 0.265302 0.022 Uiso 1 1 calc R U . . .
C17 C 0.5166(3) 0.46454(13) 0.1477(3) 0.0268(6) Uani 1 1 d . . . . .
H17A H 0.441659 0.476834 0.082104 0.040 Uiso 1 1 calc R U . . .
H17B H 0.508195 0.421854 0.161842 0.040 Uiso 1 1 calc R U . . .
H17C H 0.604092 0.472014 0.132557 0.040 Uiso 1 1 calc R U . . .
C18 C 0.3662(3) 0.60370(15) 0.3780(3) 0.0297(7) Uani 1 1 d . . . . .
H18A H 0.283855 0.612750 0.316228 0.045 Uiso 1 1 calc R U . . .
H18B H 0.363686 0.625691 0.445921 0.045 Uiso 1 1 calc R U . . .
H18C H 0.370017 0.560728 0.393693 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4926(3) 0.62230(12) 0.3439(2) 0.0177(5) Uani 1 1 d . . . . .
H19 H 0.575239 0.613252 0.408368 0.021 Uiso 1 1 calc R U . . .
C20 C 0.4925(3) 0.68907(13) 0.3183(3) 0.0266(6) Uani 1 1 d . . . . .
H20A H 0.580083 0.700188 0.306657 0.040 Uiso 1 1 calc R U . . .
H20B H 0.479142 0.711785 0.382069 0.040 Uiso 1 1 calc R U . . .
H20C H 0.418281 0.698065 0.249887 0.040 Uiso 1 1 calc R U . . .
C21 C 0.7298(3) 0.66381(14) 0.0357(3) 0.0265(6) Uani 1 1 d . . . . .
H21A H 0.735091 0.639657 -0.028972 0.040 Uiso 1 1 calc R U . . .
H21B H 0.817672 0.662427 0.094700 0.040 Uiso 1 1 calc R U . . .
H21C H 0.708313 0.705240 0.011488 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C23 1.756(3) . ?
Cl2 C23 1.752(3) . ?
Cl3 C23 1.751(4) . ?
C23 H23 1.0000 . ?
S1 O2 1.435(2) . ?
S1 O3 1.429(2) . ?
S1 O4 1.434(2) . ?
S1 C22 1.822(3) . ?
F1 C22 1.319(4) . ?
F2 C22 1.328(4) . ?
F3 C22 1.333(4) . ?
P1 C1 1.779(3) . ?
P1 C8 1.769(3) . ?
P1 C16 1.816(3) . ?
P1 C19 1.824(3) . ?
O1 C6 1.381(3) . ?
O1 C7 1.363(3) . ?
C1 C2 1.412(4) . ?
C1 C6 1.383(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(4) . ?
C7 C8 1.350(4) . ?
C7 C21 1.492(4) . ?
C8 C9 1.498(3) . ?
C9 C10 1.396(4) . ?
C9 C14 1.391(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.527(4) . ?
C16 H16 1.0000 . ?
C16 C17 1.525(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C19 1.530(4) . ?
C19 H19 1.0000 . ?
C19 C20 1.528(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C23 H23 108.4 . . ?
Cl2 C23 Cl1 111.16(19) . . ?
Cl2 C23 H23 108.4 . . ?
Cl3 C23 Cl1 110.82(19) . . ?
Cl3 C23 Cl2 109.66(18) . . ?
Cl3 C23 H23 108.4 . . ?
O2 S1 C22 103.09(15) . . ?
O3 S1 O2 115.41(15) . . ?
O3 S1 O4 114.85(15) . . ?
O3 S1 C22 103.26(16) . . ?
O4 S1 O2 114.53(14) . . ?
O4 S1 C22 103.32(14) . . ?
F1 C22 S1 111.7(2) . . ?
F1 C22 F2 107.0(3) . . ?
F1 C22 F3 107.7(3) . . ?
F2 C22 S1 111.7(2) . . ?
F2 C22 F3 106.7(3) . . ?
F3 C22 S1 111.7(2) . . ?
C1 P1 C16 109.15(13) . . ?
C1 P1 C19 109.96(12) . . ?
C8 P1 C1 102.62(12) . . ?
C8 P1 C16 112.94(12) . . ?
C8 P1 C19 111.42(12) . . ?
C16 P1 C19 110.45(12) . . ?
C7 O1 C6 123.0(2) . . ?
C2 C1 P1 121.6(2) . . ?
C6 C1 P1 119.3(2) . . ?
C6 C1 C2 119.1(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
O1 C6 C1 124.9(2) . . ?
O1 C6 C5 114.2(3) . . ?
C1 C6 C5 120.9(3) . . ?
O1 C7 C21 109.5(2) . . ?
C8 C7 O1 125.6(2) . . ?
C8 C7 C21 125.0(3) . . ?
C7 C8 P1 120.7(2) . . ?
C7 C8 C9 121.9(2) . . ?
C9 C8 P1 117.33(19) . . ?
C10 C9 C8 120.9(2) . . ?
C14 C9 C8 119.9(2) . . ?
C14 C9 C10 119.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
P1 C16 H16 106.6 . . ?
C15 C16 P1 113.92(19) . . ?
C15 C16 H16 106.6 . . ?
C17 C16 P1 110.45(19) . . ?
C17 C16 C15 112.2(2) . . ?
C17 C16 H16 106.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
P1 C19 H19 108.2 . . ?
C18 C19 P1 110.56(19) . . ?
C18 C19 H19 108.2 . . ?
C20 C19 P1 109.61(19) . . ?
C20 C19 C18 111.9(2) . . ?
C20 C19 H19 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C22 F1 -55.9(3) . . . . ?
O2 S1 C22 F2 -175.7(2) . . . . ?
O2 S1 C22 F3 64.8(3) . . . . ?
O3 S1 C22 F1 64.6(3) . . . . ?
O3 S1 C22 F2 -55.2(3) . . . . ?
O3 S1 C22 F3 -174.7(2) . . . . ?
O4 S1 C22 F1 -175.5(2) . . . . ?
O4 S1 C22 F2 64.7(3) . . . . ?
O4 S1 C22 F3 -54.7(3) . . . . ?
P1 C1 C2 C3 177.7(2) . . . . ?
P1 C1 C6 O1 4.3(4) . . . . ?
P1 C1 C6 C5 -177.0(2) . . . . ?
P1 C8 C9 C10 -64.8(3) . . . . ?
P1 C8 C9 C14 111.0(3) . . . . ?
O1 C7 C8 P1 -1.2(4) . . . . ?
O1 C7 C8 C9 177.1(2) . . . . ?
C1 P1 C8 C7 15.1(3) . . . . ?
C1 P1 C8 C9 -163.3(2) . . . . ?
C1 P1 C16 C15 -175.0(2) . . . . ?
C1 P1 C16 C17 57.6(2) . . . . ?
C1 P1 C19 C18 62.5(2) . . . . ?
C1 P1 C19 C20 -61.4(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C1 C6 O1 -176.8(3) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 O1 177.7(3) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
C6 O1 C7 C8 -15.7(4) . . . . ?
C6 O1 C7 C21 164.4(2) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
C7 O1 C6 C1 13.8(4) . . . . ?
C7 O1 C6 C5 -165.0(3) . . . . ?
C7 C8 C9 C10 116.9(3) . . . . ?
C7 C8 C9 C14 -67.3(4) . . . . ?
C8 P1 C1 C2 164.9(2) . . . . ?
C8 P1 C1 C6 -16.2(2) . . . . ?
C8 P1 C16 C15 71.6(2) . . . . ?
C8 P1 C16 C17 -55.8(2) . . . . ?
C8 P1 C19 C18 175.55(19) . . . . ?
C8 P1 C19 C20 51.7(2) . . . . ?
C8 C9 C10 C11 174.4(3) . . . . ?
C8 C9 C14 C13 -174.7(3) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C9 C14 C13 1.2(4) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C9 0.1(5) . . . . ?
C14 C9 C10 C11 -1.4(4) . . . . ?
C16 P1 C1 C2 44.9(3) . . . . ?
C16 P1 C1 C6 -136.3(2) . . . . ?
C16 P1 C8 C7 132.4(2) . . . . ?
C16 P1 C8 C9 -45.9(2) . . . . ?
C16 P1 C19 C18 -58.1(2) . . . . ?
C16 P1 C19 C20 178.06(19) . . . . ?
C19 P1 C1 C2 -76.5(3) . . . . ?
C19 P1 C1 C6 102.4(2) . . . . ?
C19 P1 C8 C7 -102.6(2) . . . . ?
C19 P1 C8 C9 79.1(2) . . . . ?
C19 P1 C16 C15 -54.0(2) . . . . ?
C19 P1 C16 C17 178.63(19) . . . . ?
C21 C7 C8 P1 178.7(2) . . . . ?
C21 C7 C8 C9 -3.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.502
_oxdiff_exptl_absorpt_empirical_full_min 0.615
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qyl-35
_database_code_depnum_ccdc_archive 'CCDC 2354057'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-03-30
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H25 O P'
_chemical_formula_sum            'C29 H25 O P'
_chemical_formula_weight         420.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N P'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.16530(10)
_cell_length_b                   15.5130(2)
_cell_length_c                   13.4254(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.7320(10)
_cell_angle_gamma                90
_cell_volume                     2188.84(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12832
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5080
_cell_measurement_theta_min      4.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16480
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.430
_diffrn_reflns_theta_min         4.472
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    106.00 143.00   0.50    0.20    --  104.75-169.00 -57.00   74
  2  ω     95.00 120.00   0.50    0.10    --   48.13-169.00 -57.00   50
  3  ω     80.00 174.00   0.50    0.20    --  104.75 125.00-120.00  188
  4  ω     53.00 115.00   0.50    0.10    --   48.13 169.00 -41.00  124
  5  ω     82.00 174.00   0.50    0.20    --  104.75 125.00  30.00  184
  6  ω    -20.00  24.00   0.50    0.10    --   48.13 -19.00   0.00   88
  7  ω     35.00 105.00   0.50    0.20    --  104.75 -99.00  90.00  140
  8  ω     42.00 105.00   0.50    0.20    --  104.75-115.00  85.00  126
  9  ω     25.00  50.00   0.50    0.10    --   48.13-115.00  85.00   50
 10  ω    -25.00  26.00   0.50    0.10    --  -48.13  19.00   0.00  102
 11  ω    -58.00 -33.00   0.50    0.20    -- -104.00  57.00   0.00   50
 12  ω    -77.00 -32.00   0.50    0.20    -- -104.00  77.00 150.00   90
 13  ω    -64.00 -34.00   0.50    0.20    -- -104.00  57.00 150.00   60
 14  ω    -64.00 -37.00   0.50    0.20    -- -104.00  57.00 120.00   54
 15  ω    -64.00 -35.00   0.50    0.20    -- -104.00  57.00 -30.00   58
 16  ω    -64.00 -32.00   0.50    0.20    -- -104.00  57.00 -60.00   64
 17  ω    -41.00  22.00   0.50    0.10    --  -48.13  38.00 -60.00  126
 18  ω    -60.00 -34.00   0.50    0.20    -- -104.00  57.00-150.00   52
 19  ω   -127.00-101.00   0.50    0.20    -- -104.00 -19.00 -90.00   52
 20  ω   -175.00-150.00   0.50    0.20    -- -104.00 -19.00 -90.00   50
 21  ω   -169.00-143.00   0.50    0.20    -- -104.00 -19.00  30.00   52
 22  ω   -168.00 -81.00   0.50    0.20    -- -104.00-115.00  85.00  174
 23  ω   -118.00 -47.00   0.50    0.10    --  -48.13-169.00 -57.00  142
 24  ω    -98.00 -73.00   0.50    0.20    -- -104.00-169.00 -57.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0772556000
_diffrn_orient_matrix_UB_12      -0.0630620000
_diffrn_orient_matrix_UB_13      0.0431278000
_diffrn_orient_matrix_UB_21      -0.0845524000
_diffrn_orient_matrix_UB_22      0.0750637000
_diffrn_orient_matrix_UB_23      0.0119135000
_diffrn_orient_matrix_UB_31      -0.0914341000
_diffrn_orient_matrix_UB_32      -0.0160494000
_diffrn_orient_matrix_UB_33      -0.1133729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4190
_reflns_number_total             4430
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+1.3657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.70599(4) 0.64557(2) 0.24233(3) 0.02705(11) Uani 1 1 d . . . . .
O1 O 0.72455(11) 0.56657(7) 0.18625(9) 0.0352(3) Uani 1 1 d . . . . .
C1 C 0.48399(14) 0.78304(10) 0.29004(12) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.51966(16) 0.84361(11) 0.37257(15) 0.0417(4) Uani 1 1 d . . . . .
H2 H 0.573807 0.890108 0.369769 0.050 Uiso 1 1 calc R U . . .
C3 C 0.47742(18) 0.83675(13) 0.45757(15) 0.0501(5) Uani 1 1 d . . . . .
H3 H 0.502581 0.878459 0.512552 0.060 Uiso 1 1 calc R U . . .
C4 C 0.39886(18) 0.76971(14) 0.46333(14) 0.0491(5) Uani 1 1 d . . . . .
H4 H 0.367848 0.766208 0.520962 0.059 Uiso 1 1 calc R U . . .
C5 C 0.36540(16) 0.70754(12) 0.38471(13) 0.0381(4) Uani 1 1 d . . . . .
H5 H 0.313038 0.660660 0.389826 0.046 Uiso 1 1 calc R U . . .
C6 C 0.40735(14) 0.71267(10) 0.29817(12) 0.0294(3) Uani 1 1 d . . . . .
C7 C 0.37401(14) 0.64559(9) 0.21466(12) 0.0275(3) Uani 1 1 d . . . . .
C8 C 0.27347(15) 0.58759(10) 0.20048(13) 0.0330(3) Uani 1 1 d . . . . .
H8 H 0.224501 0.590470 0.246116 0.040 Uiso 1 1 calc R U . . .
C9 C 0.24429(16) 0.52620(10) 0.12119(15) 0.0393(4) Uani 1 1 d . . . . .
H9 H 0.175798 0.487394 0.113000 0.047 Uiso 1 1 calc R U . . .
C10 C 0.31418(16) 0.52092(11) 0.05375(14) 0.0392(4) Uani 1 1 d . . . . .
H10 H 0.293215 0.479392 -0.001484 0.047 Uiso 1 1 calc R U . . .
C11 C 0.41524(16) 0.57703(10) 0.06778(13) 0.0346(3) Uani 1 1 d . . . . .
H11 H 0.464430 0.573018 0.022403 0.041 Uiso 1 1 calc R U . . .
C12 C 0.44581(14) 0.63920(9) 0.14734(11) 0.0276(3) Uani 1 1 d . . . . .
C13 C 0.55676(14) 0.69984(10) 0.16166(12) 0.0300(3) Uani 1 1 d . . . . .
H13 H 0.563103 0.708464 0.089788 0.036 Uiso 1 1 calc R U . . .
C14 C 0.52919(14) 0.78750(10) 0.19827(13) 0.0326(3) Uani 1 1 d . . . . .
C15 C 0.53923(16) 0.86025(11) 0.14646(16) 0.0440(4) Uani 1 1 d . . . . .
C16 C 0.5885(2) 0.86101(14) 0.05470(17) 0.0593(6) Uani 1 1 d . . . . .
H16A H 0.646549 0.812314 0.061241 0.089 Uiso 1 1 calc R U . . .
H16B H 0.633973 0.915098 0.055097 0.089 Uiso 1 1 calc R U . . .
H16C H 0.516866 0.856104 -0.011815 0.089 Uiso 1 1 calc R U . . .
C17 C 0.4997(2) 0.94823(12) 0.1715(2) 0.0606(6) Uani 1 1 d . . . . .
H17A H 0.445046 0.942124 0.214904 0.091 Uiso 1 1 calc R U . . .
H17B H 0.452821 0.978082 0.105527 0.091 Uiso 1 1 calc R U . . .
H17C H 0.575514 0.981688 0.210453 0.091 Uiso 1 1 calc R U . . .
C18 C 0.65187(15) 0.53750(10) 0.38076(13) 0.0336(3) Uani 1 1 d . . . . .
H18 H 0.632098 0.498401 0.322987 0.040 Uiso 1 1 calc R U . . .
C19 C 0.63718(17) 0.51227(11) 0.47501(14) 0.0405(4) Uani 1 1 d . . . . .
H19 H 0.608022 0.455788 0.481892 0.049 Uiso 1 1 calc R U . . .
C20 C 0.66485(17) 0.56912(12) 0.55893(14) 0.0410(4) Uani 1 1 d . . . . .
H20 H 0.653183 0.552027 0.622984 0.049 Uiso 1 1 calc R U . . .
C21 C 0.70964(15) 0.65109(11) 0.54989(13) 0.0358(4) Uani 1 1 d . . . . .
H21 H 0.729137 0.689907 0.607915 0.043 Uiso 1 1 calc R U . . .
C22 C 0.72597(14) 0.67644(10) 0.45651(12) 0.0300(3) Uani 1 1 d . . . . .
H22 H 0.757930 0.732317 0.450924 0.036 Uiso 1 1 calc R U . . .
C23 C 0.69561(13) 0.62011(10) 0.37048(12) 0.0272(3) Uani 1 1 d . . . . .
C24 C 0.83501(14) 0.72164(10) 0.26196(11) 0.0286(3) Uani 1 1 d . . . . .
C25 C 0.83822(15) 0.80528(10) 0.30215(12) 0.0321(3) Uani 1 1 d . . . . .
H25 H 0.769034 0.825727 0.321647 0.039 Uiso 1 1 calc R U . . .
C26 C 0.94201(16) 0.85835(11) 0.31359(13) 0.0358(4) Uani 1 1 d . . . . .
H26 H 0.943295 0.915198 0.340225 0.043 Uiso 1 1 calc R U . . .
C27 C 1.04379(16) 0.82869(12) 0.28628(13) 0.0393(4) Uani 1 1 d . . . . .
H27 H 1.115296 0.864885 0.295189 0.047 Uiso 1 1 calc R U . . .
C28 C 1.04131(16) 0.74642(12) 0.24607(14) 0.0391(4) Uani 1 1 d . . . . .
H28 H 1.110675 0.726532 0.226424 0.047 Uiso 1 1 calc R U . . .
C29 C 0.93801(15) 0.69273(11) 0.23427(12) 0.0325(3) Uani 1 1 d . . . . .
H29 H 0.937348 0.636068 0.207245 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4891(11) . ?
P1 C13 1.8546(16) . ?
P1 C23 1.8068(15) . ?
P1 C24 1.8112(15) . ?
C1 C2 1.404(2) . ?
C1 C6 1.414(2) . ?
C1 C14 1.482(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C6 C7 1.482(2) . ?
C7 C8 1.401(2) . ?
C7 C12 1.400(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(2) . ?
C12 C13 1.515(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.512(2) . ?
C14 C15 1.350(2) . ?
C15 C16 1.509(3) . ?
C15 C17 1.507(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C18 C23 1.395(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(2) . ?
C24 C25 1.401(2) . ?
C24 C29 1.397(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(2) . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C13 109.23(7) . . ?
O1 P1 C23 111.48(7) . . ?
O1 P1 C24 111.73(7) . . ?
C23 P1 C13 108.75(7) . . ?
C23 P1 C24 107.91(7) . . ?
C24 P1 C13 107.63(7) . . ?
C2 C1 C6 118.27(16) . . ?
C2 C1 C14 122.63(16) . . ?
C6 C1 C14 119.01(13) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.10(18) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.43(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.70(18) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.03(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 119.19(14) . . ?
C5 C6 C1 119.40(15) . . ?
C5 C6 C7 121.41(15) . . ?
C8 C7 C6 122.61(14) . . ?
C12 C7 C6 119.08(13) . . ?
C12 C7 C8 118.31(14) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.12(15) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.43(15) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.15(15) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.07(16) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C13 119.74(13) . . ?
C11 C12 C7 119.91(14) . . ?
C11 C12 C13 120.35(14) . . ?
P1 C13 H13 106.4 . . ?
C12 C13 P1 109.09(10) . . ?
C12 C13 H13 106.4 . . ?
C14 C13 P1 117.36(11) . . ?
C14 C13 C12 110.61(13) . . ?
C14 C13 H13 106.4 . . ?
C1 C14 C13 113.07(13) . . ?
C15 C14 C1 125.31(16) . . ?
C15 C14 C13 121.51(16) . . ?
C14 C15 C16 122.93(18) . . ?
C14 C15 C17 124.08(19) . . ?
C17 C15 C16 112.97(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C23 120.20(16) . . ?
C23 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.10(16) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.14(16) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.12(16) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.16(15) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 P1 115.61(12) . . ?
C18 C23 C22 119.26(14) . . ?
C22 C23 P1 125.12(12) . . ?
C25 C24 P1 125.10(12) . . ?
C29 C24 P1 115.97(12) . . ?
C29 C24 C25 118.92(14) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.27(15) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.20(16) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 119.99(15) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.33(16) . . ?
C29 C28 H28 119.8 . . ?
C24 C29 H29 119.9 . . ?
C28 C29 C24 120.28(15) . . ?
C28 C29 H29 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C13 C14 C1 -76.13(15) . . . . ?
P1 C13 C14 C15 107.33(16) . . . . ?
P1 C24 C25 C26 -179.78(12) . . . . ?
P1 C24 C29 C28 179.77(12) . . . . ?
O1 P1 C13 C12 60.78(12) . . . . ?
O1 P1 C13 C14 -172.45(11) . . . . ?
O1 P1 C23 C18 -26.43(13) . . . . ?
O1 P1 C23 C22 154.45(12) . . . . ?
O1 P1 C24 C25 172.97(12) . . . . ?
O1 P1 C24 C29 -7.12(14) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C7 C8 -162.39(14) . . . . ?
C1 C6 C7 C12 18.0(2) . . . . ?
C1 C14 C15 C16 178.74(16) . . . . ?
C1 C14 C15 C17 -3.0(3) . . . . ?
C2 C1 C6 C5 2.7(2) . . . . ?
C2 C1 C6 C7 -176.92(13) . . . . ?
C2 C1 C14 C13 142.21(15) . . . . ?
C2 C1 C14 C15 -41.4(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 178.85(15) . . . . ?
C5 C6 C7 C8 18.0(2) . . . . ?
C5 C6 C7 C12 -161.63(14) . . . . ?
C6 C1 C2 C3 -2.4(2) . . . . ?
C6 C1 C14 C13 -34.35(19) . . . . ?
C6 C1 C14 C15 142.03(16) . . . . ?
C6 C7 C8 C9 179.48(14) . . . . ?
C6 C7 C12 C11 -179.45(13) . . . . ?
C6 C7 C12 C13 0.7(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C7 C12 C13 P1 96.32(14) . . . . ?
C7 C12 C13 C14 -34.21(18) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
C8 C7 C12 C13 -178.90(13) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
C10 C11 C12 C13 179.87(14) . . . . ?
C11 C12 C13 P1 -83.49(15) . . . . ?
C11 C12 C13 C14 145.98(14) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
C12 C13 C14 C1 49.90(17) . . . . ?
C12 C13 C14 C15 -126.64(16) . . . . ?
C13 P1 C23 C18 94.05(12) . . . . ?
C13 P1 C23 C22 -85.07(14) . . . . ?
C13 P1 C24 C25 53.07(15) . . . . ?
C13 P1 C24 C29 -127.02(12) . . . . ?
C13 C14 C15 C16 -5.2(2) . . . . ?
C13 C14 C15 C17 173.10(16) . . . . ?
C14 C1 C2 C3 -178.97(15) . . . . ?
C14 C1 C6 C5 179.41(14) . . . . ?
C14 C1 C6 C7 -0.2(2) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C19 C18 C23 P1 -178.29(12) . . . . ?
C19 C18 C23 C22 0.9(2) . . . . ?
C19 C20 C21 C22 0.4(2) . . . . ?
C20 C21 C22 C23 1.0(2) . . . . ?
C21 C22 C23 P1 177.46(12) . . . . ?
C21 C22 C23 C18 -1.6(2) . . . . ?
C23 P1 C13 C12 -61.08(12) . . . . ?
C23 P1 C13 C14 65.69(13) . . . . ?
C23 P1 C24 C25 -64.14(14) . . . . ?
C23 P1 C24 C29 115.77(12) . . . . ?
C23 C18 C19 C20 0.5(2) . . . . ?
C24 P1 C13 C12 -177.74(10) . . . . ?
C24 P1 C13 C14 -50.97(13) . . . . ?
C24 P1 C23 C18 -149.47(11) . . . . ?
C24 P1 C23 C22 31.41(15) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C24 C29 C28 -0.3(2) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C26 C27 C28 C29 -0.9(3) . . . . ?
C27 C28 C29 C24 0.6(2) . . . . ?
C29 C24 C25 C26 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.692
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qyl-39
_database_code_depnum_ccdc_archive 'CCDC 2354058'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-03-20
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H25 O P'
_chemical_formula_sum            'C26 H25 O P'
_chemical_formula_weight         384.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.0883(6)
_cell_length_b                   6.3238(2)
_cell_length_c                   21.6180(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.454(4)
_cell_angle_gamma                90
_cell_volume                     2073.83(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6391
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      75.8790
_cell_measurement_theta_min      4.3230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13907
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.767
_diffrn_reflns_theta_min         2.913
_diffrn_ambient_temperature      153.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    143.00 168.00   0.50    0.30    --  104.75 125.00-180.00   50
  2  ω    132.00 171.00   0.50    0.30    --  104.75 125.00-150.00   78
  3  ω     85.00 117.00   0.50    0.30    --  104.75 125.00-180.00   64
  4  ω     88.00 124.00   0.50    0.30    --  104.75 125.00-150.00   72
  5  ω     44.00 108.00   0.50    0.15    --   47.88  32.00 -39.00  128
  6  ω    100.00 127.00   0.50    0.30    --  104.75 125.00 150.00   54
  7  ω    136.00 165.00   0.50    0.30    --  104.75 125.00 150.00   58
  8  ω     98.00 126.00   0.50    0.30    --  104.75  32.00 -39.00   56
  9  ω     33.00  68.00   0.50    0.30    --  104.75 -57.00-150.00   70
 10  ω     34.00  67.00   0.50    0.30    --  104.75 -57.00-180.00   66
 11  ω     36.00  67.00   0.50    0.30    --  104.75 -57.00-120.00   62
 12  ω    -12.00  14.00   0.50    0.15    --   47.88 -19.00   0.00   52
 13  ω      6.00  38.00   0.50    0.15    --   47.88 -32.00 160.00   64
 14  ω     34.00  61.00   0.50    0.30    --  104.75 -57.00 150.00   54
 15  ω     34.00  59.00   0.50    0.30    --  104.75 -57.00 -60.00   50
 16  ω     36.00  85.00   0.50    0.30    --  104.75 -99.00 -60.00   98
 17  ω    -33.00  25.00   0.50    0.15    --  -47.88  32.00 -39.00  116
 18  ω     38.00 106.00   0.50    0.30    --  104.75 -99.00-180.00  136
 19  ω    -23.00  24.00   0.50    0.15    --  -47.88  38.00  90.00   94
 20  ω   -117.00 -39.00   0.50    0.15    --  -47.88 -32.00 160.00  156
 21  ω    -64.00 -33.00   0.50    0.30    -- -104.00  57.00  30.00   62
 22  ω    -64.00 -32.00   0.50    0.30    -- -104.00  57.00   0.00   64
 23  ω    -64.00 -32.00   0.50    0.30    -- -104.00  57.00-120.00   64
 24  ω    -62.00 -34.00   0.50    0.30    -- -104.00  57.00  60.00   56
 25  ω    -60.00 -34.00   0.50    0.30    -- -104.00  57.00  90.00   52
 26  ω    -64.00 -38.00   0.50    0.30    -- -104.00  57.00 150.00   52
 27  ω   -174.00 -93.00   0.50    0.30    -- -104.00 -32.00 160.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213091000
_diffrn_orient_matrix_UB_12      0.0506149000
_diffrn_orient_matrix_UB_13      -0.0628191000
_diffrn_orient_matrix_UB_21      -0.0936969000
_diffrn_orient_matrix_UB_22      0.0890878000
_diffrn_orient_matrix_UB_23      -0.0320424000
_diffrn_orient_matrix_UB_31      0.0328728000
_diffrn_orient_matrix_UB_32      0.2209604000
_diffrn_orient_matrix_UB_33      0.0272494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3413
_reflns_number_total             4158
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0768P)²+1.8822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1727
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.24909(4) 0.71295(11) 0.49492(3) 0.0426(2) Uani 1 1 d . . . . .
O1 O 0.24163(13) 0.9466(3) 0.49539(10) 0.0545(5) Uani 1 1 d . . . . .
C1 C 0.11567(17) 0.3803(4) 0.60035(13) 0.0447(6) Uani 1 1 d . . . . .
C2 C 0.09679(19) 0.1827(5) 0.57199(15) 0.0545(7) Uani 1 1 d . . . . .
H2 H 0.125785 0.135267 0.542779 0.065 Uiso 1 1 calc R U . . .
C3 C 0.0357(2) 0.0530(6) 0.58589(18) 0.0679(9) Uani 1 1 d . . . . .
H3 H 0.023344 -0.083101 0.566402 0.081 Uiso 1 1 calc R U . . .
C4 C -0.0069(2) 0.1212(6) 0.62784(19) 0.0724(10) Uani 1 1 d . . . . .
H4 H -0.048579 0.031906 0.637385 0.087 Uiso 1 1 calc R U . . .
C5 C 0.0106(2) 0.3177(6) 0.65587(18) 0.0676(9) Uani 1 1 d . . . . .
H5 H -0.019680 0.365391 0.684185 0.081 Uiso 1 1 calc R U . . .
C6 C 0.07239(19) 0.4471(5) 0.64308(15) 0.0560(7) Uani 1 1 d . . . . .
H6 H 0.085339 0.581842 0.663482 0.067 Uiso 1 1 calc R U . . .
C7 C 0.18280(16) 0.5199(4) 0.58681(13) 0.0416(6) Uani 1 1 d . . . . .
C8 C 0.17440(17) 0.5669(4) 0.52451(13) 0.0461(6) Uani 1 1 d . . . . .
H8 H 0.122436 0.516561 0.492015 0.055 Uiso 1 1 calc R U . . .
C9 C 0.25868(16) 0.5862(4) 0.64421(12) 0.0405(5) Uani 1 1 d . . . . .
C10 C 0.28558(18) 0.7863(4) 0.65254(13) 0.0460(6) Uani 1 1 d . . . . .
H10 H 0.250889 0.890092 0.623549 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3681(2) 0.8562(5) 0.70548(15) 0.0565(7) Uani 1 1 d . . . . .
H11A H 0.351751 0.933617 0.739572 0.068 Uiso 1 1 calc R U . . .
H11B H 0.400814 0.954949 0.686501 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4273(2) 0.6731(5) 0.73700(17) 0.0643(8) Uani 1 1 d . . . . .
H12A H 0.457571 0.621076 0.706883 0.077 Uiso 1 1 calc R U . . .
H12B H 0.472864 0.721683 0.777846 0.077 Uiso 1 1 calc R U . . .
C13 C 0.3753(2) 0.4960(6) 0.75263(16) 0.0649(9) Uani 1 1 d . . . . .
H13A H 0.346129 0.547174 0.783549 0.078 Uiso 1 1 calc R U . . .
H13B H 0.415679 0.379552 0.774207 0.078 Uiso 1 1 calc R U . . .
C14 C 0.30578(19) 0.4131(5) 0.69061(15) 0.0528(7) Uani 1 1 d . . . . .
H14A H 0.334463 0.317365 0.667582 0.063 Uiso 1 1 calc R U . . .
H14B H 0.261894 0.329272 0.703144 0.063 Uiso 1 1 calc R U . . .
C15 C 0.36115(17) 0.6250(4) 0.53701(13) 0.0452(6) Uani 1 1 d . . . . .
C16 C 0.4262(2) 0.7787(5) 0.54997(16) 0.0589(7) Uani 1 1 d . . . . .
H16 H 0.410382 0.921999 0.538853 0.071 Uiso 1 1 calc R U . . .
C17 C 0.5140(2) 0.7245(6) 0.57906(18) 0.0707(9) Uani 1 1 d . . . . .
H17 H 0.558355 0.830460 0.588141 0.085 Uiso 1 1 calc R U . . .
C18 C 0.5369(2) 0.5173(6) 0.59471(16) 0.0677(9) Uani 1 1 d . . . . .
H18 H 0.597062 0.479619 0.614721 0.081 Uiso 1 1 calc R U . . .
C19 C 0.4726(2) 0.3642(6) 0.58140(16) 0.0643(8) Uani 1 1 d . . . . .
H19 H 0.488883 0.221085 0.592402 0.077 Uiso 1 1 calc R U . . .
C20 C 0.38446(19) 0.4152(5) 0.55223(14) 0.0522(7) Uani 1 1 d . . . . .
H20 H 0.340553 0.308210 0.542761 0.063 Uiso 1 1 calc R U . . .
C21 C 0.22419(17) 0.6136(4) 0.41190(13) 0.0431(6) Uani 1 1 d . . . . .
C22 C 0.22461(18) 0.7589(5) 0.36406(14) 0.0509(7) Uani 1 1 d . . . . .
H22 H 0.239326 0.902154 0.376022 0.061 Uiso 1 1 calc R U . . .
C23 C 0.2040(2) 0.6989(5) 0.29926(15) 0.0589(8) Uani 1 1 d . . . . .
H23 H 0.204317 0.800299 0.266918 0.071 Uiso 1 1 calc R U . . .
C24 C 0.1830(2) 0.4923(6) 0.28186(15) 0.0612(8) Uani 1 1 d . . . . .
H24 H 0.168296 0.450835 0.237259 0.073 Uiso 1 1 calc R U . . .
C25 C 0.1831(2) 0.3447(5) 0.32858(16) 0.0655(9) Uani 1 1 d . . . . .
H25 H 0.168615 0.201709 0.316117 0.079 Uiso 1 1 calc R U . . .
C26 C 0.2042(2) 0.4037(5) 0.39408(15) 0.0565(7) Uani 1 1 d . . . . .
H26 H 0.204913 0.301203 0.426374 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.483(2) . ?
P1 C8 1.794(3) . ?
P1 C15 1.815(3) . ?
P1 C21 1.816(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.395(4) . ?
C1 C7 1.497(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.341(4) . ?
C7 C9 1.482(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.330(4) . ?
C9 C14 1.508(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.502(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.503(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.524(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.386(4) . ?
C15 C20 1.388(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(4) . ?
C21 C26 1.389(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.370(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(4) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C8 116.44(12) . . ?
O1 P1 C15 111.77(13) . . ?
O1 P1 C21 111.10(12) . . ?
C8 P1 C15 109.57(13) . . ?
C8 P1 C21 102.75(12) . . ?
C15 P1 C21 104.17(12) . . ?
C2 C1 C6 118.9(3) . . ?
C2 C1 C7 120.9(2) . . ?
C6 C1 C7 120.2(3) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C1 119.3(2) . . ?
C8 C7 C9 123.9(2) . . ?
C9 C7 C1 116.7(2) . . ?
P1 C8 H8 116.0 . . ?
C7 C8 P1 128.1(2) . . ?
C7 C8 H8 116.0 . . ?
C7 C9 C14 116.3(2) . . ?
C10 C9 C7 121.5(2) . . ?
C10 C9 C14 122.1(2) . . ?
C9 C10 H10 118.4 . . ?
C9 C10 C11 123.3(3) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.5(3) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.0(3) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.0(3) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C9 C14 C13 113.2(3) . . ?
C9 C14 H14A 108.9 . . ?
C9 C14 H14B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 P1 116.3(2) . . ?
C16 C15 C20 119.7(3) . . ?
C20 C15 P1 123.8(2) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 119.1(3) . . ?
C19 C20 H20 120.5 . . ?
C22 C21 P1 117.0(2) . . ?
C22 C21 C26 119.0(3) . . ?
C26 C21 P1 124.0(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.6(3) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C15 C16 C17 -176.9(3) . . . . ?
P1 C15 C20 C19 176.7(2) . . . . ?
P1 C21 C22 C23 -178.1(2) . . . . ?
P1 C21 C26 C25 177.8(2) . . . . ?
O1 P1 C8 C7 -83.5(3) . . . . ?
O1 P1 C15 C16 -14.2(3) . . . . ?
O1 P1 C15 C20 170.3(2) . . . . ?
O1 P1 C21 C22 16.1(2) . . . . ?
O1 P1 C21 C26 -163.2(2) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C7 C8 P1 -175.1(2) . . . . ?
C1 C7 C9 C10 -133.3(3) . . . . ?
C1 C7 C9 C14 49.3(3) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C1 C7 C8 55.0(4) . . . . ?
C2 C1 C7 C9 -121.0(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C1 C7 C8 -126.3(3) . . . . ?
C6 C1 C7 C9 57.7(3) . . . . ?
C7 C1 C2 C3 178.7(3) . . . . ?
C7 C1 C6 C5 -179.7(3) . . . . ?
C7 C9 C10 C11 -172.7(3) . . . . ?
C7 C9 C14 C13 -172.7(2) . . . . ?
C8 P1 C15 C16 -144.8(2) . . . . ?
C8 P1 C15 C20 39.6(3) . . . . ?
C8 P1 C21 C22 141.3(2) . . . . ?
C8 P1 C21 C26 -38.0(3) . . . . ?
C8 C7 C9 C10 50.9(4) . . . . ?
C8 C7 C9 C14 -126.5(3) . . . . ?
C9 C7 C8 P1 0.6(4) . . . . ?
C9 C10 C11 C12 13.8(4) . . . . ?
C10 C9 C14 C13 10.0(4) . . . . ?
C10 C11 C12 C13 -45.7(4) . . . . ?
C11 C12 C13 C14 60.5(4) . . . . ?
C12 C13 C14 C9 -41.9(4) . . . . ?
C14 C9 C10 C11 4.4(4) . . . . ?
C15 P1 C8 C7 44.5(3) . . . . ?
C15 P1 C21 C22 -104.4(2) . . . . ?
C15 P1 C21 C26 76.3(3) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C15 C20 C19 1.3(4) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C15 -0.7(5) . . . . ?
C20 C15 C16 C17 -1.1(5) . . . . ?
C21 P1 C8 C7 154.8(3) . . . . ?
C21 P1 C15 C16 105.8(2) . . . . ?
C21 P1 C15 C20 -69.7(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C22 C21 C26 C25 -1.5(4) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
C24 C25 C26 C21 0.8(5) . . . . ?
C26 C21 C22 C23 1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.937
_oxdiff_exptl_absorpt_empirical_full_min 0.670
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qyl_43
_database_code_depnum_ccdc_archive 'CCDC 2378927'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-08-16
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C28 H24 O2 P'
_chemical_formula_sum            'C29 H24 F3 O5 P S'
_chemical_formula_weight         572.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5096(6)
_cell_length_b                   15.4521(8)
_cell_length_c                   16.5422(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.04(4)
_cell_angle_gamma                90
_cell_volume                     2686.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.285
_cell_measurement_theta_min      2.860
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1148 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.7532.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29596
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.279
_diffrn_reflns_theta_min         3.915
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4641
_reflns_number_total             4817
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+1.9863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27250(4) 0.25748(3) 0.31182(3) 0.02381(14) Uani 1 1 d . . . . .
F1 F 0.16588(14) 0.11537(9) 0.36991(8) 0.0462(3) Uani 1 1 d . . . . .
F2 F 0.18039(12) 0.11876(8) 0.24040(8) 0.0386(3) Uani 1 1 d . . . . .
F3 F 0.34608(12) 0.09475(8) 0.31171(9) 0.0442(3) Uani 1 1 d . . . . .
O3 O 0.34011(13) 0.26724(10) 0.38692(8) 0.0308(3) Uani 1 1 d . . . . .
O4 O 0.34798(14) 0.27076(10) 0.24003(9) 0.0335(3) Uani 1 1 d . . . . .
O5 O 0.14746(13) 0.29593(10) 0.31057(9) 0.0328(3) Uani 1 1 d . . . . .
C29 C 0.23899(19) 0.14112(14) 0.30860(12) 0.0288(4) Uani 1 1 d . . . . .
P1 P 0.72360(4) 0.29434(3) 0.47089(3) 0.01578(13) Uani 1 1 d . . . . .
O1 O 0.77744(12) 0.47184(8) 0.50813(8) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.46589(12) 0.25312(8) 0.55394(8) 0.0226(3) Uani 1 1 d . . . . .
C1 C 0.62703(16) 0.36406(11) 0.52963(10) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.66513(17) 0.45061(12) 0.54417(10) 0.0204(4) Uani 1 1 d . . . . .
C3 C 0.59170(18) 0.50486(12) 0.59160(11) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.617232 0.562905 0.601326 0.029 Uiso 1 1 calc R U . . .
C4 C 0.47935(19) 0.47252(13) 0.62485(11) 0.0271(4) Uani 1 1 d . . . . .
H4 H 0.428630 0.509462 0.657552 0.033 Uiso 1 1 calc R U . . .
C5 C 0.43961(19) 0.38871(13) 0.61178(11) 0.0259(4) Uani 1 1 d . . . . .
H5 H 0.362916 0.368034 0.635242 0.031 Uiso 1 1 calc R U . . .
C6 C 0.51361(17) 0.33511(11) 0.56375(10) 0.0197(4) Uani 1 1 d . . . . .
C7 C 0.52466(17) 0.18969(11) 0.51040(11) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.63717(16) 0.19613(11) 0.47152(10) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.69525(16) 0.12113(11) 0.42691(11) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.79383(18) 0.07356(12) 0.46127(12) 0.0247(4) Uani 1 1 d . . . . .
H10 H 0.824728 0.088673 0.513358 0.030 Uiso 1 1 calc R U . . .
C11 C 0.84756(19) 0.00410(13) 0.42010(13) 0.0310(5) Uani 1 1 d . . . . .
H11 H 0.914498 -0.027974 0.444425 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8045(2) -0.01857(13) 0.34431(13) 0.0320(5) Uani 1 1 d . . . . .
H12 H 0.841401 -0.065970 0.316234 0.038 Uiso 1 1 calc R U . . .
C13 C 0.7073(2) 0.02838(14) 0.30982(13) 0.0358(5) Uani 1 1 d . . . . .
H13 H 0.677084 0.013074 0.257619 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6527(2) 0.09792(13) 0.35042(12) 0.0297(4) Uani 1 1 d . . . . .
H14 H 0.585948 0.129754 0.325671 0.036 Uiso 1 1 calc R U . . .
C15 C 0.44386(19) 0.11052(12) 0.51387(13) 0.0296(4) Uani 1 1 d . . . . .
H15A H 0.447795 0.085646 0.568305 0.044 Uiso 1 1 calc R U . . .
H15B H 0.475003 0.068085 0.474543 0.044 Uiso 1 1 calc R U . . .
H15C H 0.355628 0.125785 0.501040 0.044 Uiso 1 1 calc R U . . .
C16 C 0.87347(16) 0.27940(11) 0.51979(11) 0.0191(4) Uani 1 1 d . . . . .
C17 C 0.87516(18) 0.28573(13) 0.60404(11) 0.0255(4) Uani 1 1 d . . . . .
H17 H 0.800841 0.303045 0.632444 0.031 Uiso 1 1 calc R U . . .
C18 C 0.9856(2) 0.26666(14) 0.64586(12) 0.0306(5) Uani 1 1 d . . . . .
H18 H 0.986869 0.270171 0.703186 0.037 Uiso 1 1 calc R U . . .
C19 C 1.09452(19) 0.24238(13) 0.60413(13) 0.0280(4) Uani 1 1 d . . . . .
H19 H 1.170526 0.230117 0.633032 0.034 Uiso 1 1 calc R U . . .
C20 C 1.09301(18) 0.23596(12) 0.52098(13) 0.0265(4) Uani 1 1 d . . . . .
H20 H 1.168064 0.219513 0.492909 0.032 Uiso 1 1 calc R U . . .
C21 C 0.98231(18) 0.25343(12) 0.47804(12) 0.0228(4) Uani 1 1 d . . . . .
H21 H 0.980762 0.247760 0.420867 0.027 Uiso 1 1 calc R U . . .
C22 C 0.74025(16) 0.33155(11) 0.36872(10) 0.0183(4) Uani 1 1 d . . . . .
C23 C 0.84554(18) 0.37854(12) 0.34131(12) 0.0251(4) Uani 1 1 d . . . . .
H23 H 0.915072 0.389546 0.376538 0.030 Uiso 1 1 calc R U . . .
C24 C 0.8479(2) 0.40892(14) 0.26259(13) 0.0331(5) Uani 1 1 d . . . . .
H24 H 0.919372 0.440521 0.243528 0.040 Uiso 1 1 calc R U . . .
C25 C 0.7461(2) 0.39324(14) 0.21178(12) 0.0326(5) Uani 1 1 d . . . . .
H25 H 0.748252 0.414110 0.157777 0.039 Uiso 1 1 calc R U . . .
C26 C 0.6411(2) 0.34742(13) 0.23869(11) 0.0287(4) Uani 1 1 d . . . . .
H26 H 0.571462 0.337261 0.203316 0.034 Uiso 1 1 calc R U . . .
C27 C 0.63765(17) 0.31639(12) 0.31728(11) 0.0214(4) Uani 1 1 d . . . . .
H27 H 0.565748 0.284961 0.335973 0.026 Uiso 1 1 calc R U . . .
C28 C 0.8263(2) 0.55739(13) 0.52187(15) 0.0366(5) Uani 1 1 d . . . . .
H28A H 0.904541 0.565451 0.490563 0.055 Uiso 1 1 calc R U . . .
H28B H 0.844686 0.564881 0.579517 0.055 Uiso 1 1 calc R U . . .
H28C H 0.762885 0.600213 0.504891 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4391(14) . ?
S1 O4 1.4428(15) . ?
S1 O5 1.4424(14) . ?
S1 C29 1.833(2) . ?
F1 C29 1.333(2) . ?
F2 C29 1.331(2) . ?
F3 C29 1.335(2) . ?
P1 C1 1.7705(17) . ?
P1 C8 1.7687(18) . ?
P1 C16 1.7857(18) . ?
P1 C22 1.7937(17) . ?
O1 C2 1.362(2) . ?
O1 C28 1.436(2) . ?
O2 C6 1.372(2) . ?
O2 C7 1.364(2) . ?
C1 C2 1.417(3) . ?
C1 C6 1.393(2) . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C7 C8 1.350(2) . ?
C7 C15 1.490(3) . ?
C8 C9 1.503(2) . ?
C9 C10 1.392(3) . ?
C9 C14 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.397(3) . ?
C16 C21 1.395(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.399(3) . ?
C22 C27 1.393(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 115.10(9) . . ?
O3 S1 O5 114.78(9) . . ?
O3 S1 C29 102.87(9) . . ?
O4 S1 C29 102.78(9) . . ?
O5 S1 O4 115.50(9) . . ?
O5 S1 C29 103.21(9) . . ?
F1 C29 S1 112.42(14) . . ?
F1 C29 F3 107.23(17) . . ?
F2 C29 S1 111.61(14) . . ?
F2 C29 F1 107.50(16) . . ?
F2 C29 F3 106.46(16) . . ?
F3 C29 S1 111.30(14) . . ?
C1 P1 C16 109.61(8) . . ?
C1 P1 C22 112.22(8) . . ?
C8 P1 C1 102.96(8) . . ?
C8 P1 C16 109.84(8) . . ?
C8 P1 C22 109.31(8) . . ?
C16 P1 C22 112.48(8) . . ?
C2 O1 C28 117.51(15) . . ?
C7 O2 C6 124.08(14) . . ?
C2 C1 P1 120.37(13) . . ?
C6 C1 P1 121.18(14) . . ?
C6 C1 C2 118.44(16) . . ?
O1 C2 C1 113.44(15) . . ?
O1 C2 C3 125.85(17) . . ?
C3 C2 C1 120.70(17) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.61(18) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.09(17) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.78(18) . . ?
C6 C5 H5 120.6 . . ?
O2 C6 C1 124.15(16) . . ?
O2 C6 C5 114.48(16) . . ?
C5 C6 C1 121.37(17) . . ?
O2 C7 C15 108.14(15) . . ?
C8 C7 O2 126.53(16) . . ?
C8 C7 C15 125.32(17) . . ?
C7 C8 P1 121.07(14) . . ?
C7 C8 C9 122.19(16) . . ?
C9 C8 P1 116.74(12) . . ?
C10 C9 C8 120.59(16) . . ?
C14 C9 C8 121.04(16) . . ?
C14 C9 C10 118.36(17) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.65(18) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.55(19) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.12(18) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.86(19) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 120.46(19) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 P1 117.01(14) . . ?
C21 C16 P1 122.42(14) . . ?
C21 C16 C17 120.23(17) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.66(18) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.06(19) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.37(18) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.37(18) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 120.4 . . ?
C20 C21 C16 119.29(18) . . ?
C20 C21 H21 120.4 . . ?
C23 C22 P1 123.29(14) . . ?
C27 C22 P1 116.49(13) . . ?
C27 C22 C23 120.10(17) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.66(18) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.94(19) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.73(18) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 119.94(19) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 120.2 . . ?
C26 C27 C22 119.63(18) . . ?
C26 C27 H27 120.2 . . ?
O1 C28 H28A 109.5 . . ?
O1 C28 H28B 109.5 . . ?
O1 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 C29 F1 61.80(16) . . . . ?
O3 S1 C29 F2 -177.32(13) . . . . ?
O3 S1 C29 F3 -58.53(16) . . . . ?
O4 S1 C29 F1 -178.33(14) . . . . ?
O4 S1 C29 F2 -57.45(15) . . . . ?
O4 S1 C29 F3 61.34(16) . . . . ?
O5 S1 C29 F1 -57.89(16) . . . . ?
O5 S1 C29 F2 63.00(15) . . . . ?
O5 S1 C29 F3 -178.21(14) . . . . ?
P1 C1 C2 O1 1.0(2) . . . . ?
P1 C1 C2 C3 -178.45(14) . . . . ?
P1 C1 C6 O2 -1.5(2) . . . . ?
P1 C1 C6 C5 178.05(14) . . . . ?
P1 C8 C9 C10 78.32(19) . . . . ?
P1 C8 C9 C14 -101.26(19) . . . . ?
P1 C16 C17 C18 173.84(15) . . . . ?
P1 C16 C21 C20 -174.56(14) . . . . ?
P1 C22 C23 C24 -176.50(15) . . . . ?
P1 C22 C27 C26 176.58(14) . . . . ?
O1 C2 C3 C4 -179.32(16) . . . . ?
O2 C7 C8 P1 -1.7(3) . . . . ?
O2 C7 C8 C9 178.34(16) . . . . ?
C1 P1 C8 C7 0.82(17) . . . . ?
C1 P1 C8 C9 -179.18(13) . . . . ?
C1 P1 C16 C17 28.84(17) . . . . ?
C1 P1 C16 C21 -157.89(15) . . . . ?
C1 P1 C22 C23 98.02(16) . . . . ?
C1 P1 C22 C27 -77.82(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 O2 179.64(16) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 O2 -179.67(16) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C6 O2 C7 C8 0.9(3) . . . . ?
C6 O2 C7 C15 -179.94(16) . . . . ?
C6 C1 C2 O1 179.84(15) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 O2 C6 C1 0.9(3) . . . . ?
C7 O2 C6 C5 -178.71(16) . . . . ?
C7 C8 C9 C10 -101.7(2) . . . . ?
C7 C8 C9 C14 78.7(2) . . . . ?
C8 P1 C1 C2 179.47(14) . . . . ?
C8 P1 C1 C6 0.63(16) . . . . ?
C8 P1 C16 C17 -83.60(16) . . . . ?
C8 P1 C16 C21 89.67(16) . . . . ?
C8 P1 C22 C23 -148.41(15) . . . . ?
C8 P1 C22 C27 35.75(16) . . . . ?
C8 C9 C10 C11 179.93(17) . . . . ?
C8 C9 C14 C13 -179.98(19) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
C15 C7 C8 P1 179.29(15) . . . . ?
C15 C7 C8 C9 -0.7(3) . . . . ?
C16 P1 C1 C2 62.62(16) . . . . ?
C16 P1 C1 C6 -116.22(15) . . . . ?
C16 P1 C8 C7 117.51(15) . . . . ?
C16 P1 C8 C9 -62.49(15) . . . . ?
C16 P1 C22 C23 -26.13(18) . . . . ?
C16 P1 C22 C27 158.03(13) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C16 C21 C20 -1.5(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C16 1.4(3) . . . . ?
C21 C16 C17 C18 0.4(3) . . . . ?
C22 P1 C1 C2 -63.11(16) . . . . ?
C22 P1 C1 C6 118.06(15) . . . . ?
C22 P1 C8 C7 -118.64(15) . . . . ?
C22 P1 C8 C9 61.36(15) . . . . ?
C22 P1 C16 C17 154.42(14) . . . . ?
C22 P1 C16 C21 -32.31(18) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C27 -0.3(3) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C27 C22 C23 C24 -0.8(3) . . . . ?
C28 O1 C2 C1 -177.77(16) . . . . ?
C28 O1 C2 C3 1.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
